Methyl iodide → 4-Benzyloxy-2-methoxybenzaldehyde

To a 100 mL RB flask fitted with magnetic stirrer was charged with 10 mL of acetonitrile. To the stirred solvent were added 4-(benzyloxy)-2-hydroxybenzaldehyde (1.0 g, 4.38 mmol), potassium carbonate (1.21 g, 8.76 mmol). The reaction mixture was brought to 0° C., was added methyl iodide (1.135 g, 8.76 mmol) in acetonitrile (5 mL) drop wise and stirred at room temperature for 16 h. The reaction mixture was concentrated to distill off the solvent. The residue was extracted with ethyl acetate (50 mL). The organic layer was washed with water (40 mL) and saturated brine solution (40 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product obtained as a white solid (1.06 g, yield: 100.0%).

1. customTo a 100 mL RB flask fitted with magnetic stirrer
2. customwas brought to 0° C.
3. concentrationThe reaction mixture was concentrated
4. distillationto distill off the solvent
5. extractionThe residue was extracted with ethyl acetate (50 mL)
6. washThe organic layer was washed with water (40 mL) and saturated brine solution (40 mL)
7. dry with materialThe organic layer was dried over anhydrous Na2SO4
8. customthe solvent was removed under reduced pressure

ORD record

ord-7bde54a000014bf58f71b87d9aeae0e5

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2